1-Iodopropane → 1-Propylpiperidin-4-ol

HRID 1760968Notes

Reaction equation

HRID 1760968 reaction equation
I[CH2:2][CH2:3][CH3:4].[OH:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1>CC(C)=O>[OH:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:2][CH2:3][CH3:4])[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 336431-IodopropaneHCID 79341Piperidin-4-ol

Product 1

HCID 136652691-Propylpiperidin-4-ol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Iodopropane (22 ml) was added dropwise during 15 minutes to a stirred suspension of 4-hydroxypiperidine (20 g) in acetone (250 ml) and the resultant mixture was stirred at ambient temperature for 20 hours. The mixture was evaporated and the residue was partitioned between diethyl ether and 2N aqueous sodium hydroxide solution. The organic phase was washed with brine, dried over magnesium sulphate and evaporated to give 4-hydroxy-N-propylpiperidine as an oil (19.6 g); NMR Spectrum: (DMSOd6) 0.82 (t, 3H), 1.16 (m, 4H), 1.66 (m, 2H), 1.91 (m, 2H), 2.06 (t, 2H), 2.64 (m, 2H), 3.38 (m, 1H), 4.45 (d, 1H); Mass Spectrum: M+H+ 144.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between diethyl ether and 2N aqueous sodium hydroxide solution
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-cc68eb2293d64394bf31adfbe3250c66
Source dataset
uspto-grants-2005_01
Patent number
US06846827B1

Reaction notes

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